Direct Report Keeps Asking “Why?” Ask Madeleine

March 18, 2023 Madeleine Homan Blanchard


Dear Madeleine,

I manage a large regional business unit, and a few years ago all managers went through a coaching class. We learned to ask fewer why questions when coaching, and I have found it to be a helpful tip. I know it’s generally not a good idea to ask why questions, because they can put people on the defensive.

What is your advice on what to do when someone asks a why question?

I was recently asked one by a manager who works for me, who also went through the training and should know better.

I find myself not wanting to answer the question for fear I will appear defensive by even answering. I don’t see a good or productive way to answer the question, mainly because the way it was asked seemed to presume that I had done something wrong.

Is it rude to reframe the question the into a form I could answer? Like a politician?

This incident has made me realize that I seem to get a lot of these kinds of questions from this manager—questions I would prefer she answer for herself. It makes me concerned that she either can’t answer the questions or is kicking the questions up a level for some reason. Maybe she is asking for more support?

Confused and Confronted Leader


Dear Confused and Confronted Leader,

This is an interesting one! For readers who wonder what is being discussed here, you can get some background from this article: Important Coaching Techniques Every Leader Should Practice. In most coaching skills programs, ours included, a fundamental is to ask better questions. This means, by and large, to ask what and how questions, as they tend to produce more useful answers. And it is true that why questions tend to put people on the defensive.

In your case, it is hard to formulate an answer without more detail, so I will proceed with general principles that hopefully pertain to your situation.

  • Asking why questions when one should know better is simply a habit. I wouldn’t read too much into it. You might suggest that the why question be asked as a what or a how question.
  • Just because someone asks a question doesn’t mean you have to answer it. If someone really needs an answer they will probably follow up and ask the question differently, or ask a different question altogether.
  • The best way to respond to any question that makes you feel defensive is with curiosity. I guess you can always reframe the question, but you might try answering a tricky question with another question. For example: To respond to “Why was my team not told about this decision beforehand?” you might ask “What is happening among your team that concerns you?”
  • One rule of thumb to consider whenever you feel defensive is to never take anything personally. You could ask yourself “How might I see this differently if I weren’t feeling attacked?”

The situation where your direct report keeps coming to you with questions she should be able to answer herself seems like a perfect opportunity to put on your coach hat. When anyone comes to you with questions you know in your heart they have the answers to, you can evoke their wisdom and simply ask (nicely of course) what they think the answer is. Either they will have good answers or you will discover they need a lot more direction than you realized. It is entirely possible your people do not see the big picture or have forgotten the reasons for a change being made. As a leader, you have to remember that anything you think is obvious, is not.

Finally, it sounds like you are uncomfortable with your people challenging you or doubting your authority. But it is better to have people around you who do that than a bunch of “yes” people who praise every decision and laugh at all of your jokes. That spells doom for any leader.

If your people seem to doubt your authority, you can always rely on the world’s best questions from our Conversational Capacity Program:

  • What am I not seeing that you’re seeing?
  • What’s your take on this idea?
  • What does it look like from your angle?
  • Are you seeing something I am missing?

Maybe they are doubting your authority and you would be well served to listen to them. Or maybe they just don’t understand and need you to spend more time explaining your thinking. Either way, they will be much more likely to have your back.

I hope there is something in here you can use.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.


About the Author

Madeleine Homan Blanchard

Madeleine Homan Blanchard is a Master Certified Coach and cofounder of Blanchard Coaching Services. She is coauthor of Blanchard’s Coaching Essentials training program, and several books including Leverage Your Best, Ditch the Rest, Coaching in Organizations, and Coaching for Leadership.

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